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If I had a nickel for every time I’ve been asked or explained how to style boots well, I would not be sitting and writing this from my cute little writing nook in my closet. Don’t get me wrong I love my little space and being shut out from the rest of the world, but yea If I had those nickels, I would be The Ibiza Hippie shopping the markets on a Wednesday afternoon or in Santorini eating fresh caught seafood and dancing amongst the pink bougainvillea after sipping on Ouza. Where else do you think I would be? I know I know, we just met. You couldn’t know. Fun fact is that my former self used to work for a pretty popular footwear brand. The truth is in the last 21 years 15 of those have been in the footwear industry. Yep, you could just consider me and Old Shoe Dog only I’m not a shoe or a dog and while I may take a jab at my age, I’m actually not old and pretty sure I never will be old. Basically, most of my career and my life have been all about how to style that damn boot. It was all about who is going to wear it, where are they wearing it, and of course the how are they going to wear it?
FYI, thanks to AI imagery software, we’re able to create very specific fashion and hairstyle examples to illustrate the points being made. In some cases, imagery is exaggerated to hammer home the point.
If we talk boots we talk love.
Boots were my first fashion true love. Or was it my true nemesis in actuality? Not only was I eager to enter this world two months early but my parents soon realized that I was walking with my feet pointing inward. They yeah, I had to get a brace to correct it as a wee little concha, but I wasn’t having it. Apparently, I used to try to take them off all the time, I don’t remember but I can see myself doing something like that. Anyway, my Mom was, is and will always be a special kind of smart. That little 20-year-old decided that it might help me, and I might be more tolerant if I wore my shoes on the wrong feet to turn then out!! Think about it, makes total sense. Guess what? It totally worked. My walk was totally corrected. It is I promise…I mean I might have a slight turn in of my right foot after a long day of walking, or if I’ve had more than one old fashioned. So maybe my fascination set in then, and maybe that’s why I worked in footwear for the better part of my career. Maybe it was destiny.
First pairs.
My first favorite pair of footwear was a boot. A little pair of red cowboy boots. I remember stomping around in them in my little ivory baby doll dress with rainbow trim (my rainbow love, I tell ya goes deep). I loved these boots. You can imagine how traumatized I was when our German Shepard Sandy nibbled the toes and ruined them. I was crying and not because Sandy nibbled them when they were on my feet but because my pretty red boots had teeth marks in them. I think my parents replaced them but not totally sure, but I do know that last year I did get another pair of red cowboy boots. I’m sure it won’t be my last.
Boots are my literal jam. Not really because that’s not possible and gross but I’m trying to be a little dramatic here. Maybe it’s better to say that I’ve been obsessed by boots and really footwear in general. I’m not special in this way, but I’ve had a pretty good darn good time getting into some boots and shoes.
My first four loves.
Listen boots are how we built this world! You can wear them any way you’d like. I’m not here to say you can’t wear short boots with yoga pants or tall boots with long dresses. You can and you’ll look fabulous. I am just here to tell you how I love to style my boots and booties.
Let’s not get physical.
Now, I’m going to say a word and you are going to feel some sorta way about but sometimes it’s good to feel some ways. Leg warmers. Mmmm hmmm, I said it but honestly these are a boots friend. I love to throw on a pair and have them peep just over the top. Depending on how much room you have in the calf you can slightly scrunch them, or even fold them over but even just being there it adds just a touch of something different. I’m such a fan that when I couldn’t find the right ones I cut off the sleaves to a vintage sweater because I loved the knit and color so I wore them as legwarmers. I wouldn’t even just keep these beauties for the tall ones…they’re super cute with a shorter boot. It’s winter people, layer is the key and it’s cute. If you live in a cold climate and you haven’t added them to your wardrobe yet, ya probably should consider it. You are going to thank me later. I wore a pair of duck boots the other day because it had been raining for days and I was walking around a lake, but I put on my oatmeal-colored leg warmers with my oatmeal-colored beanie and my funky bright poncho and I dunno but it was a fun outfit day. I felt good. I was also warm; they were practical, and they just worked. I got some compliments too. Cute, I know!
Now, the only time I would probably pass is when the boots are a little more tailored. Who needs that added calf bulk?
Boots and embellishments.
Only boots here babes. If the style is a little more refined play around with the ankle. Give it a little twist like braiding some thin leather pieces or soft jute and wrap it around, it could be a chain or anything really. It’s alright if you add a little jingle to your jangle. I love a little pop of color and don’t even get me started on a flower. Who says you can’t add your own style to a pair of boots? Old or new!
Sock it to me.
What do I love more than a boot and dress combo? Boots and socks, socks and boots. I’m obsessed with little peak a boo detail. Lace on top? Ok. Glitter trim? Yes, please. This might just be my love language…but a dainty passive trimmed sock paired with an overly aggressive combat boot you know how I love a good fashion contradiction.
Fancy lady.
So maybe all this goes out the window because you need something a bit more formal. Tights baby tight! I do not mean plain tights in any color nope not even black. Do I wear it, sure of course but if I can I try to wear that something different black tight? Don’t be afraid to add some pattern and yes even if it doesn’t match perfectly. We are beyond the matchy matchy, and trust me that took a lot of retail therapy to admit. Say it again. We are beyond matchy matchy. I would go sweater knit or glitter stars and skip the seam in the back. I would opt in for a bold floral if the rest of your outfit is all black and skip the basic. Remember friends don’t let friends wear fishnets unless it’s Halloween and then only maybe.
Your type's signature aesthetic, color palette, and capsule wardrobe — in one guide.
The important thing is to think outside the shoe box! Bring a little piece of your sole or is it soul to your outfit. Let them see your light shine through footwear. Style it, don’t let it style you.
The day you think you have that fashion flop is the day you have inspired someone you don’t even know.
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